Portrait of Jason (Holliday) Could Be Shirley Clarke's Masterpiece

"I used to work [while wearing] sunglasses," laughs Jason Holliday (né Aron Payne) in the documentary Portrait of Jason. "That was so they couldn't see what I was thinking." Though speaking of his specific circumstances working as a houseboy for often racist bosses, Holliday also—in two succinct lines—lays bare the survival tactic at the core of that most imitated and misunderstood of cultural commodities: black American cool. The roles of affect and artifice in mediating the realities of racism, homophobia, and poverty are perhaps the true subjects of Shirley Clarke's landmark doc, now gorgeously restored by the technicians at Milestone Film.

Shot over the course of 12 booze-fueled hours one night in December 1966, and released the next year, Portrait could be Clarke's masterpiece. Early champions included Allen Ginsberg and Ingmar Bergman, who called it "the most extraordinary film I've seen in my life." Clad in a dark jacket, white shirt, slacks, and round-rim glasses that glamorously set off his face, Holliday (oh so ready for his close-up) alternately stands against a sparsely appointed mantle, lounges on the floor against a chair, or flops onto a sofa, a drink almost always in hand as he drops anecdote after outlandish anecdote.

He's a self-professed hustler with dreams of stardom: "I'm a stone whore," he grins. "And I'm not ashamed of it." He holds the camera with the intensity of a Hollywood pro as he recounts his childhood: violent, homophobic father; a mother about whom he's ambivalent. He covers the subcultural milieus he's inhabited (prisons, mental institutions, the heady queer and queen cultures of Harlem and San Francisco); the tortured history of his nightclub act; and his friendships with jazz legends Miles Davis and Carmen McRae. The abundance of tales and the wisdom he distills from them seem to add at least a decade to the age (33) he claims on camera, and there's a weatheredness to Holliday's face and eyes that suggests the wear of experience.

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Holliday is often magnetic, but he's almost as frequently tedious. The latter quality does nothing to diminish his overall magnetism—or the prescience of his being. He's a figure that foreshadows today's reality-celebrity complex, although his wit and intelligence elevate him above the Real Housewives and other human detritus.

But just as interesting as Holliday are Clarke and her co-interviewer, Carl Lee, both heard off-camera. Clarke famously identified with black culture because she felt like an outsider in white America. That identification has rarely been dissected, just reflexively cited to afford her hipster/counterculture cred. But Portrait complicates that in fascinating and disturbing ways. When Jason remarks on how he's suffered, Clarke scoffs from the sidelines, "You're not suffering," oblivious to all she's truly captured. At one point during a lull in his storytelling, she barks, "What else ya got?"

Lee's interactions with Jason are even more revealing, fraught with an unexplained backstory that is filled with homoerotic tension from Jason's end, but disdain and dismissiveness from Lee's. At one point, Jason is dismantling the insecurities that have tormented him, saying, "They told me I was cute. I thought I was the ugliest thing in town." Lee commands, "Talk about the nickel-and-dime shit, not about being cute." It's the Negro trickster he wants, the entertainment that is spun from black pain, not serious consideration of that pain. And that, of course, is the demand at the heart of the consumption of that most imitated and misunderstood of American cultural commodities: black cool.